Middleton Homes under $300,000

Welcome to Middleton, Wisconsin – a charming city that beautifully blends suburban tranquility with vibrant urban life. Nestled in Dane County, just minutes from the bustling capital of Madison, Middleton is known for its picturesque landscapes, friendly community, and top-notch amenities. With its scenic parks, delightful dining options, and a strong sense of community, it’s no wonder that Middleton is often referred to as one of the best places to live in the state.

For homebuyers searching for affordability without sacrificing quality, Middleton offers a variety of homes under $300,000. This is an excellent opportunity for first-time buyers, families, or anyone looking to invest in a thriving area. These homes provide a perfect balance of comfort and style, featuring charming designs, spacious layouts, and beautifully landscaped yards. Whether you're seeking a cozy single-family home, a modern townhouse, or a quaint condo, Middleton has options that cater to diverse tastes and budgets.

In addition to its attractive real estate, Middleton boasts a strong school system, numerous recreational opportunities, and a rich cultural scene. Residents enjoy easy access to numerous parks, biking trails, and outdoor activities, making it an ideal location for those who love to stay active. Plus, with a variety of shopping and dining options, you’ll never run out of things to do.

If you’re looking for a welcoming community with affordable housing options, Middleton is the perfect place to call home. Embrace the lifestyle that this delightful city has to offer, and discover your dream home today!

Newest Middleton Homes under $300,000

6230 Middleton Springs Dr Unit 6230, Middleton

$289,000

2 Beds ⋅ 2 Baths ⋅ 2033394 MLS ⋅ ACTIVE Status

Open floor plan lit by the sun at several angles. Upper level 2 bedroom, 2 bath with private deck. Great location with easy access to shopping. Private garage and laundry. Middleton schools.

6230 Middleton Springs Dr Unit 6230, Middleton

$254,900

2 Beds ⋅ 1 Baths ⋅ 2033126 MLS ⋅ ACTIVE Status

Great location in the Middleton-Cross Plains School District and just minutes from downtown Madison! This well-maintained, 2 bedroom, Condo features a gourmet kitchen with cherry cabinets, granite countertops, tile backsplash & stainless steel appliances. Convenient in-unit washer/dryer. Enjoy the spacious balcony with beautiful views of Lake Mendota and Marshall Park. Walk to Lakeview Park with splash pad, tennis courts, and baseball fields. A wonderful combination of location, convenience and views!

2051 Allen Blvd Unit 401, Middleton

2814 Pleasant View Rd Unit 202, Middleton

$250,000

2 Beds ⋅ 1 Baths ⋅ 2031873 MLS ⋅ ACTIVE UNDER CONTRACT Status

Enjoy easy condo living in a fantastic Middleton location! This bright and spacious 2nd-floor unit sits directly across from Firefighter’s Memorial Park and features abundant natural light and an open-concept layout perfect for everyday living and entertaining. Step outside to your private balcony for morning coffee or a relaxing evening outdoors. Both bedrooms offer generous space, including a walk-in closet in the primary. Additional conveniences include in-unit laundry, a private garage, and an extra-large storage unit. Located in the sought-after Middleton-Cross Plains School District with quick access to parks, shopping, schools, dining, and the Beltline. Professionally managed condo association with pets and rentals allowed. A great opportunity to enjoy space, convenience, and a prime Middleton location!

2814 Pleasant View Rd Unit 202, Middleton

$250,000

1 Beds ⋅ 2 Baths ⋅ 2031821 MLS ⋅ ACTIVE Status

Neat, clean, updated floors and windows, move-in ready, ranch-style condo. Floor-to-ceiling west-facing windows and doors bring in wonderful natural light and overlook the beautiful Harbor Village grounds and nearby Pheasant Branch Conservancy. In-unit washer and dryer, fireplace, and den or study off the living room. Underground parking, basement storage, basic cable, pool, tennis courts, and cabana add to the convenience. Pets permitted, subject to association rules.

3120 Creek View Dr Unit 1, Middleton

$158,500

1 Beds ⋅ 1 Baths ⋅ 2031265 MLS ⋅ ACTIVE Status

Opportunity to own in Middleton at an approachable price point! This updated 1-bedroom, 1-bath lower-level condo offers a spacious, open layout with plenty of room to relax, dine and entertain. The refreshed kitchen features white cabinetry, generous counter space, stainless steel appliances and a large peninsula overlooking the dining and living areas. Updated flooring and crisp neutral finishes carry throughout the unit for a clean, move-in-ready feel. The generously sized bedroom provides great closet space, while the full bath offers plenty of room and functionality. Whether you're looking for your first home, downsizing, or stop paying rent, this condo delivers an affordable opportunity to own in Middleton!

7401 Century Pl Unit 9, Middleton

$190,000

2 Beds ⋅ 1 Baths ⋅ 2030919 MLS ⋅ ACTIVE Status

Currently leased through May 2027 at $1,520/month — this is a rare opportunity: a rentable condo in desirable Middleton, ideal for investors or an owner occupant. This tastefully updated, well-maintained first-floor 2-bedroom, 1-bath condo offers comfortable living with a practical, easy-to-maintain layout. The location is a standout, with convenient access to Hilldale shopping, scenic trails, conservancies, parks, and Lake Mendota, plus everyday amenities close by. Outdoor lovers will appreciate having the water and green space close by, year-round. A straight shot to downtown Madison means commuting is simple. This property offers an attractive, turnkey opportunity for investors seeking an established rental in a sought-after area, combining location, condition, and long-term rental potential.

7106 Fortune Dr Unit 3, Middleton

$299,900

3 Beds ⋅ 2 Baths ⋅ 2030645 MLS ⋅ ACTIVE Status

Adjacent to Pheasant Branch Conservancy, this large Middleton 3-bedroom, 2 full baths, updated condo could be all yours! Surrounded by Cedar Trees, with a ground-level patio offering lush greenery & privacy. Great common space w/ a Gazebo, Warm underground parking, private storage unit, & large storage locker. Water Softener and Filters maintained by Maintenance; this unit has extra storage, including its own washer & dryer. Full Kitchen Remodel, floor plan has been opened up, newly remodeled & designed for efficiency, easy living, & lots of natural light throughout! See list of improvements in Associated Docs. This building is well cared for by its association; owners have gratitude for the beautiful community found here. Easy Access to Downtown Middleton/Madison. Bus Stops at Driveway. Easy access to hiking and biking in Pheasant Branch. Short walk to Lake Mendota & Mendota County Park. Located a few blocks from Dane Co. best restaurants & Shops. Dues include high-speed internet

3412 Valley Ridge Rd Unit 4, Middleton

$269,900

1 Beds ⋅ 1 Baths ⋅ 2029617 MLS ⋅ ACTIVE Status

Your rent era is OVER! This 1-bedroom, 1-bath Middleton condo is a fresh way to make the move into homeownership without taking on the maintenance of a house. The open layout keeps life easy, with a breakfast bar ready for morning coffee, a gas fireplace for laid-back nights, and a sunroom that can flex from home office to chill space. Two spots in the heated underground garage mean no scraping windshields all winter, and an included storage unit gives your extras a home too. The community clubhouse adds an exercise room and extra kitchen, while the Greenway Blvd location keeps shopping, dining, recreation and daily essentials close. Less upkeep, more freedom, and a place where your monthly payment can start working toward something of your own.

8510 Greenway Blvd Unit 104, Middleton

$295,000

2 Beds ⋅ 1 Baths ⋅ 2028077 MLS ⋅ ACTIVE UNDER CONTRACT Status

Enjoy carefree condo living in highly desirable Bella Casa community! Ideally located just mins from Greenway Station, Pleasant View Golf Course, dining, parks + downtown Middleton, this light-filled residence offers exceptional combination of comfort + convenience. Open-concept floor plan features hardwood floors, spacious living room w/cozy gas fireplace, + walkout access to a private balcony. Well-appointed kitchen includes SS appliances, breakfast bar, pantry + dining area. French doors open to versatile den, ideal for a home office or extra sleeping space. Retreat to expansive primary bedroom featuring vaulted ceilings, abundant natural light, a generous walk-in closet w/ exceptional storage & spacious ensuite bath w/dual sinks, honeycomb tile flooring. Enjoy outstanding amenities including a beautiful clubhouse w/ kitchen, fitness center & billiards room. Wonderful opportunity to enjoy low-maintenance living in one of Middleton's most convenient locations.

8530 Greenway Blvd Unit 307, Middleton

$160,000

1 Beds ⋅ 1 Baths ⋅ 2027571 MLS ⋅ ACTIVE Status

Fresh, modern, and completely turnkey! This beautifully updated Middleton condo features renovations throughout, offering a clean, move-in ready space you'll love coming home to. Includes a dedicated storage unit for added convenience. Set in a vibrant, going community close to shopping, dining, and more- this is low-maintenance living at its best. (Free off-street parking, too!)

7401 Century Pl Unit 103B, Middleton

$249,900

2 Beds ⋅ 2 Baths ⋅ 2027472 MLS ⋅ ACTIVE Status

Welcome home to this beautifully renovated condo featuring spacious bedrooms and stylish updates throughout. The stunning new kitchen boasts quartz countertops, modern finishes, and flows seamlessly into the living space featuring durable luxury vinyl plank flooring throughout. Both bathrooms have been updated with modern tile, creating a clean and timeless feel. Step outside and enjoy the community's pool and well-maintained common areas, offering the perfect setting to relax or socialize. Combining modern upgrades with low-maintenance living, this move-in-ready condo is ready for a new owner! FHA/VA Approved Financing!

5538 Century Ave Unit 1, Middleton

$249,000

2 Beds ⋅ 1 Baths ⋅ 2027352 MLS ⋅ ACTIVE Status

Conveniently located near shopping, restaurants, and the bus line, this beautifully updated end-unit condo offers comfort, convenience, and investment potential. Featuring 2 bedrooms, 1 full bath, an open layout, in-unit washer and dryer, and a spacious private balcony, this home is move-in ready. Enjoy the convenience of heated underground parking with one assigned space, elevator access, and secure building amenities. Currently operating as a successful short-term rental, this property offers rental income potential through the remainder of the year. The established short-term rental business and all furnishings are available for purchase separately, providing a turnkey investment opportunity or a fully furnished personal retreat. Don't miss this versatile property in an exceptional location!

2051 Allen Blvd Unit 201, Middleton

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